On March 20, 2012, Holland signed a five-year contract with the Rangers, worth $28.5 million.

In early January 2014, he had what the team described as a "freak accident", falling down stairs at home and landing on his left knee. He underwent arthroscopic surgery on January 10th and had to miss the start of the season as a result. After the surgery, Holland explained that his dog, named "Wrigley", had pushed him while running up the stairs, causing the fall and the injury. He was limited to 6 appearances that season, all of them in September as his recovery from the surgery took some time, but was a solid 2-0, 1.46. He had a 25/5 K/W ratio in 37 innings, showing that he was back in full health. He started the Rangers' home opener on April 10, 2015, but lasted only one inning, as he had no velocity on his fastball. He was diagnosed with a strain in his left shoulder, putting him out for at least two months.